Winchester diarist Mary Greenhow Lee noted on February 26, 1863, that the weather conditions were “intolerable.” The roads were frozen and icy and “the rain on the deep snow, has made the streets impassible.” In spite of the precarious travel conditions, at 10 p.m. on the evening of February 25, Captain Frank Bond of the 1st Confederate Maryland Cavalry, along with forty men from Company A, and twenty from Company D, rode north from Strasburg along Cedar Grade Road “anxious for some excitement.”
By daybreak on Thursday the 26th, Confederate cavalrymen had advanced to the outskirts of Winchester. When the enemy came into view they “charged through an infantry picket, receiving only a few random shots. At the junction of the Cedar Creek and Staunton roads they were met by a volley of musketry from a house, but it did not check them. They turned up the Staunton road toward home, riding down a third infantry picket.”
Route Taken by the 1st Maryland Cavalry to Winchester and Kernstown.
Captain Bond’s 1st Maryland Cavalry detachment galloped south along the Valley Pike. Upon arriving at Kernstown, however, “they found a cavalry picket of 15 men quietly warming themselves in a house.” Bond ordered the house surrounded. The Confederates quickly “captured 7 men and 9 horses, and left several of the enemy dead or wounded in the house.” Triumphant in their foray, they rode swiftly toward Strasburg, “bringing off their prisoners and captured horses with a loss of only 1 man missing.”
During this time period Brigadier General Robert Milroy commanded Union forces stationed in the lower Shenandoah Valley. Milroy had occupied the town of Winchester shortly after General William “Grumble” Jones’ men had withdrawn on December 13, 1862. Notorious for his strict discipline with local civilians, General Milroy believed occupying the town was critical to controlling both the valley and the Baltimore and Ohio Railroad.
General Milroy received a report of the morning’s attack at 4:30 a.m. and reacted promptly. He “immediately sent orders for the whole of the Thirteenth Regiment Pennsylvania Cavalry and one company of the First New York Voluntary Cavalry to pursue the enemy with all possible speed.” In spite of his avowed urgency, it was 6 a.m. before designated forces were able to begin their pursuit. Milroy’s cavalry force was commanded by Major Martin Byrne, of the Thirteenth Pennsylvania Cavalry, assisted by Major Michael Kerwin, of the same regiment. All told there were more than 500 cavalrymen in the taskforce.
Union troopers “pursued the enemy with energy,” in accordance with General Milroy’s orders. They were instructed to go “as far as the cavalry camp on Strawberry Hill, 2 miles beyond Strasburg, and then to return, after learning as fully as possible the position and strength of the enemy.” The terrain feature referred to in Milroy’s orders is what is know locally as Fisher’s Hill.
The squadron of New York Cavalry (also known as the Lincoln Cavalry), numbering forty-five rank and file, was commanded by Lieutenant Passenger. The New Yorkers, and a company of the Pennsylvania cavalry under command of Captain Jacob Dewees, took the advance in the pursuit. Dewees recorded: “About 10 a.m., and about three miles beyond Strasburg, they overtook the rebel force which had threatened my pickets, attacked and dispersed them, recapturing our men and capturing some 25 or 30 of the rebels and a corresponding number of horses.”
Captain Dewees was able to extract information from his prisoners indicating the enemy was “encamped in force between Woodstock and Edinburg.” Emboldened by their success at Fisher’s Hill, Lieutenant Passenger announced he “would pursue the rebels even further in an attempt to kill or capture even more.” Captain Dewees “ordered him to desist” as to continue would be in violation of their orders. “The Lieutenant, however, turned his horse as if he had not heard the Captain’s order, and took off with his men in pursuit of the fleeing enemy.” Dewees was heard to mutter: “Let the bastard hang then.”
General Milroy noted in his official report: “At Strawberry Hill they found the enemy, attacked and drove them, rescuing my captured men and taking 11 prisoners from the enemy. With this the officer in command of my cavalry was not content, but imprudently, and in violation of orders, continued the pursuit of the fugitives to within 2 miles of Woodstock.”
Route of Union Cavalry Pursuit to Fisher’s Hill
Captain Dewees, with a portion of his command, returned with the prisoners to Strasburg, while “the remainder of his command and the detachment of New York cavalry, under Lieutenant Passenger, continued the pursuit of the rebels in the direction of Woodstock, not on the regular pike, but by a road which turns to the right some 5 miles beyond Strasburg.”
As Captain Dewees trooped north with his detainees toward Winchester, he intercepted Major Michael Kerwin and the First Battalion of the 13th Pennsylvania Cavalry. Dewees recounted everything that had transpired which seemed to please the major. Expressing concern for the safety of Lieutenant Passenger and his command, Kerwin decided he would ride on to reinforce him. With the Confederates retreating along the Back Road, he decided he would try to intercept them on the Valley Pike this side of Woodstock.
According to Colonel Oliver Funsten of the Eleventh Virginia Cavalry: “About 11.45 on the morning of the 26th ultimo, he received a dispatch from General Jones, directing me to move my regiment at once toward Woodstock, where a body of the enemy’s cavalry was supposed to be, and which was distant about 6 miles from camp. A large portion of the regiment being on detached service, and without taking time to collect a number who had permission to visit in the immediate neighborhood of camp, I marched, in a few minutes after receiving the order, with 120 men.”
With the 11th Virginia Cavalry now leading the pursuit, General Jones and Colonel Funsten rode together, north along the Valley Pike. Jones informed Funsten “he had no intention of allowing the Yankees to poke their noses into his tent.” He also stated “that the enemy were a short distance in front, and that, although their force was vastly superior, I might venture an attack.” Once the enemy’s position was “ascertained by scouts, General Jones commanded Colonel Flournoy to sound the attack.”
Colonel Flournoy “accordingly gave the order, and most gallantly was it responded to. The enemy were just beginning to retire, ignorant of our proximity.” “The Confederates charged, bugles blaring and yelling like demons, upon the poor cowardly Pennsylvaninites with pistols, carbines and sabers.” They “dashed past their rear guard, who occupied an eminence near the road, and charged the rear of the column. So sudden and impetuous was the attack that every attempt (of which there were several) made by their officers to rally and form a line was unavailing. We pressed them hotly, using both saber and revolver with good effect, to Cedar Creek Bridge, a distance of about 12 miles.”
In his official report General Milroy wrote: “The other portion of the force composing the expedition was suddenly attacked by re-enforcements from the enemy’s cavalry, stationed near Woodstock. My force immediately began a hasty and confused retreat, which only became the more confounded the longer it was continued. The major commanding succeeding in rallying but once, and then only for a moment and to no purpose, though he and most of his subordinates used the utmost endeavors to quiet the men and give the enemy battle.” It was not until they reached Cedar Creek that Major Kerwin was finally able to persuade his men to contest the enemy advance.
Map Showing the Confederate Attack at Cedar Creek
“Not far in the rear of the Eleventh in this mad ride for vengeance thundered the old Seventh.” Colonel Richard Dulany had arrived with 220 men from the 7th Virginia Cavalry. “General Jones here ordered me to move forward rapidly, as the Yankees had halted and reformed on the hill beyond the town. When we reached the high ground beyond Strasburg; we found the enemy had retired, and again formed about 300 yards south of Cedar Creek. About 130 had crossed the creek, and, as near as I could estimate, about 250 had formed to meet us.”
The 11th Virginia Cavalry presently came under accurate fire from the Pennsylvania and New York boys as they neared Cedar Creek. In early September 1862 the regiment had been issued “58 caliber muskets and pistols.” Though the muskets were awkward for cavalry to transport and handle, they could prove deadly for their opponents.
Dulany would note: “As we came in sight of each other, they seemed to advance slowly toward us, but when we got within 200 yards, our sabers drawn, and the charge ordered, their hearts failed them, and, wheeling in beautiful order, they went at full speed to the bridge, crossed, and again, formed to receive us.
“As but 2 men could cross the bridge abreast, they could easily have prevented our crossing with their long-range guns, as their position was very strong and higher than the bridge.” Dulany knew a direct assault would be suicidal. “Changing the direction of our column, we crossed the creek at the ford, some 200 yards below the bridge. As soon as a portion of my command had crossed, the enemy again broke, not waiting for us to close with them.”
Colonel Richard Dulany
Colonel Dulany recalled his men and horses were exhausted from their nineteen mile chase and assault. They “rested their horses some ten minutes, and the advantage of a start of a long and steep hill, we could not overtake them until near Middletown. The race now became truly exciting. It was a helter-skelter chase, the fastest horses in our column taking the lead. As we came up with the rear, not a man that I saw offered to surrender until driven back by the sabers of my men or shot.”
Area Where the 7th Virginia Cavalry Forded Cedar Creek
The fighting at Middletown was “hand to hand.” Lieutenant Granville of Company A led the 7th Virginia’s charge. He “personally wounded four men with his saber.” “Some, finding we were overtaking them, slipped from their horses and sought refuge in the houses along the road, and many had thrown their pistols away when captured. We captured about 70 prisoners—5 of them were too nearly dead to move or parole, and 2 others were left on the roadside, being broken down and unable to travel—53 horses, and a large number of arms.”
By 4.30 in the afternoon, General Milroy had learned from fugitives, the true scope of the disaster. He “immediately ordered forward to the theater of action the First New York Cavalry, with directions to advance until they got in rear of our fugitives and in sight of the enemy, if the enemy were still pursuing. If the enemy were in formidable numbers, this regiment was instructed to fall back until it received the support of a regiment of infantry and a section of a battery, which I advanced simultaneously with it. The New York cavalry, Major Adams commanding, advanced until it gained the rear of our fugitives, and as far as 3 miles beyond Strasburg, when, observing nothing of the enemy, in pursuance of my orders it fell back. From the above statement it will be seen that the disaster occurred in consequence of a gross violation of orders, more censurable in this particular instance from the fact that the enemy was known to be encamped in force between Woodstock and Edinburg.”
General Grumble Jones would report: “The First New York Cavalry and the Thirteenth Pennsylvania Cavalry attacked my pickets this -morning and drove them into Woodstock. I fell on them with the Eleventh and the Seventh Virginia regiments of cavalry; cut them up badly. We have about 200 prisoners, and killed and wounded many more. We carried them at a charge of full speed from 5 miles below Woodstock to Newtown. Lieutenant-Colonel [O. E.] Funsten and his regiment behaved with conspicuous gallantry.” He cited Lieutenant Granville for his courage as well.
General Milroy was enraged by the performance of his cavalry. He would write, simply: “The conduct of my cavalry, except the New York and Pennsylvania companies that left the Valley road beyond Strasburg, was disgraceful and cowardly.” John Keenan of the 13th Pennsylvania would note: “More than twenty percent of the regiment was lost in a mere skirmish with a force of less than half our size.” In addition, the regiment was “accused of cowardly behavior and gross neglect of orders.”
Meanwhile, back in Winchester Mary Greenhow Lee would note the arrival of “the remnants of the 13th Pa Cavalry.” They “came dashing in town, in miserable plight.” “No more than a dozen of the 300 who went out this morning, are left to tell the tale.”
According to widespread rumors General Milroy was so upset he decided “he was going to shell the town.” Fortunately, this did not happen, though the treatment of local citizenry would not improve as a result of the incident. Only its liberation by General Lee’s Army in June of 1863 would accomplish that.
It is interesting to note little has been written about the conflict in the Shenandoah Valley between the time of the Union occupation of Winchester in December of 1862 and the Second Battle of Winchester in June of 1863. As you can see, though Confederate forces were greatly outnumbered, there were lots of opportunities for clashes. In many cases Confederates forces were not only successful in distracting their enemy, they were able to defeat them decisively. With the natural defensive advantages offered by Cedar Creek, there would be frequent clashes in this area in the future.
Armstrong, Richard L. 7th Virginia Cavalry. H. E. Howard Inc. Lynchburg, Va. 1992.
Musick, Michael. 6th Virginia Cavalry. H. E. Howard. Lynchburg, Va. 1990.
Official Records of the Civil War. Series I – Vol XXV – Part 1.
Sharpe, Hal. Shenandoah County in the Civil War: Four Dark Years. The History Press. Charleston, S.C. 2012.
Strader, Eloise. The Civil War Journal of Mary Greenhow Lee of Winchester, Va. Winchester-Frederick County Historical Society. Winchester, Va. 2011.
Sudell, William B. Though All the World Betrays Thee. J. M. Santarelli Publishing. Glenside, Pennsylvania. 1999.
Washington, Bushrod. A History of the Laurel Brigade. The Johns Hopkins University Press. Baltimore, Md. 2002.